Chloroacetic Acid → 2-(Chloromethyl)benzothiazole

HRID 7086

反応式

HRID 7086 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[Cl:9][CH2:10][C:11](O)=[O:12].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:9][CH2:10][C:11]1[O:12][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1.[Cl:9][CH2:10][C:11]1[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

参加物

6

反応物 3

HCID 300Chloroacetic AcidHCID 87132-AminothiophenolHCID 11430Potassium Carbonate

生成物 2

HCID 3049782-(Chloromethyl)benzothiazoleHCID 20619892-(Chloromethyl)-1,3-benzoxazole

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

Using literature procedures (Addison, A. W.; Nageswara Rao, T.; Wahlgren, C. G. J. Heterocyclic Chem. 1983, 20, 1481–1484) a substituted 2-aminophenol (or a 2-aminothiophenol (5 mmol)) was mixed with chloroacetic acid (940 mg, 10 mmol) in polyphosphoric acid (5 mL), and the viscous mixture was then heated to 120° C. for 3 hours. The reaction was then cooled, and diluted with water (˜20 mL) and then neutralized with potassium carbonate to pH˜7. The mixture was then extracted with ethyl acetate, and the combined organic fractions were then dried over MgSO4 and concentrated. The residue was then purified by column chromatography on silica gel (50% ethyl acetate in hexanes) to afford the desired 2-chloromethylbenzoxazole (or 2-chloromethylbenzothiazole).

後処理

  1. temperatureThe reaction was then cooled
  2. extractionThe mixture was then extracted with ethyl acetate
  3. dry with materialthe combined organic fractions were then dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was then purified by column chromatography on silica gel (50% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-1b495aa703b04744bb5cf439eed00b5d
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

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